Find cheap flights from Illinois to Grand Cayman

Find cheap flights from Illinois to Grand Cayman

Search hundreds of travel sites at once for deals on flights to Grand Cayman

Round-trip
Economy
Boston (BOS)
Grand Cayman
Fri 5/7
Fri 5/14
Any month
Compare vs. KAYAK |

Good to know

Low season

SeptemberBest time to beat the crowds with an average 3% drop in price.

High season

DecemberMost popular time to fly with an average 3% increase in price.

Average price round-trip

$789(avg. price over the last 2 weeks)

Good deal round-trip

$388or less

Good deal one-way

$172or less

FAQs for booking flights from Illinois to Grand Cayman

How does KAYAK find such low prices on flights from Illinois to Grand Cayman?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Grand Cayman?

What is the Hacker Fare option on flights from Illinois to Grand Cayman?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Grand Cayman?

Top 3 airlines serving from Illinois to Grand Cayman

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,486 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "Tv dont work in a fly of 4hr 30 min"

Cons: "Was 2hrs behind schedule"

Pros: "Free wireless"
Cons: "I'm not in Charlotte"

Pros: "Service was awesome, 100% recommended"

Pros: "The crew was good, and they tried to make up for the delay with a gift certificate"
Cons: "More than three hours of delay because there was no crew assigned to that flight"

Cons: "The food can be better."

Pros: "Loved the roomy seats"
Cons: "Sound system was low quality. Hard to here the movie."

Pros: "Unbelievable for the price."
Cons: "Nothing bad to say."

Cons: "My first flight was delayed an hour due to pilot error (we left the gate on time, but sat on the tarmac for an hour). This caused me to miss my connecting flight, which stranded me at JFK because they only had one flight per day to my destination. JetBlue's customer service told me I could not reach my destination until the next day, which was unacceptable (I had a morning interview). In fact, the only thing they said they could do was *PARTIALLY* refund my ticket, even though they stranded me in a completely different city. They also said I would "be able to" book a new flight with a different carrier, which cost roughly $400, using my own money. In the end, I spent about an hour talking with customer service until they were "nice enough" to do a partial refund with an additional credit equaling the remainder of my $400 ticket to fly with them in the future. It was still a very poor interaction with customer service."

Pros: "Clean plane"
Cons: "Took 3+ hours to get in the plane"

Cons: "The cabin crew was a little lacking and the captain did not mentioned that we had landed almost a full hour later than scheduled."

Pros: "Pilot’s smooth take off and landing."
Cons: "The weather haha."

Pros: "It was a great trip for the cost."
Cons: "Nothing."

Pros: "Free WiFi. Cute vids for Holloween"
Cons: "Nothing!"

Pros: "Nothing"
Cons: "Being delayed from 6am to 1:30pm"

Pros: "I appreciate that they let families with strollers board after Group A, there seems to be more space than the major carriers, and the snacks are good!"
Cons: "My Satellite XM radio didn’t seem to be working."

Pros: "Seat space for each passenger"

Pros: "Turbulence, wait time before landing and staying still for long periods on bothends"

Pros: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"

Pros: "More leg room Affordable prices Snacks dunkin donut coffee Pleasant flight attendant Punctuality"
Cons: "Nothing"

Pros: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"
Cons: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"

Pros: "The crew talked a big game. They were ready for anything, including loss of cabin pressure, paid snacks, and even a water landing."
Cons: "No water landing! I was excited to float around on a hot day, go down an awesome slide, and catch some sick waves, but come on people, we never even got a chance!"

Pros: "The crews were very friendly A lot of options from direct tv and other entertainment programs The seats were wide enough Free Wifi"
Cons: "The plane got 2 hours delayed The screen was too small There was no charger on the plane Food option was limited"

Pros: "Cheerful, efficient service. No hidden costs. Free gate to gate WiFi. Comfortable seats. Never flown them before and they are now at the top of my list."
Cons: "Nothing yet."

Pros: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"

Cons: "We arrived later for almost 2 hours"

Pros: "I dont usually fly, staff was friendly and helpful, made my experience less stressful."

Cons: "my flight was delayed for 2 hours and there was no compensation for it"

Pros: "Our flight attendant Jeramy was FABULOUS!!"

Cons: "No movies just Direct TV."

Pros: "No gate, waited 2 hours in plane"

Pros: "Everything is ok"
Cons: "Not a thing"

Cons: "When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!"

Cons: "Flight was delayed by over an hour and we never got an explanation as to why. Just an apology from the pilot once we finally took off."

Cons: "Turbulence was terrible, understand that is not JetBlue issue - wanted to note."

Pros: "Captain and crew"
Cons: "Luggage handling"

Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"

Cons: "Movies didn't work and we were one hour delayed on the runway."

Pros: "The only good things about this flight were: - The crew at the gate were very friendly and attentive - We arrived safely without incident"
Cons: "We were delayed 2 times before boarding. We were delayed 1 more time while on the plane. The pilot told us there was equipment trouble that had been fixed, but there was paperwork to fill out and it would only be a few minutes...and then radio silence for 30 minutes before pulling back. The flight attendants rushed through the pre-flight announcents and I could only understand about 60% of it due to speed, volume and accent. Despite asking me for my drink order, it never came...and I only heard a few soda cans pop open at all. Did they just decide not to serve us? She even gave me a napkin for it. Luckily when they put the snack basket in front of me, there was a tiny bottle of water, which I grabbed...little did I know, that was all I would get. The flight attendants were just tapping in the back of the plane the rest of the flight. They didn’t even bother collecting garbage until we were on final approach. They also never did the normal checks before landing."

Pros: "Crew was happy and friendly"
Cons: "Can’t think of anything"

Pros: "They refund me the money"
Cons: "I almost lost my international connection, had to pay double to get my destination on time"

Pros: "Ez check in with kiosk"
Cons: "I would like to see an organic food option, even with a fee if necessary. Recommendation, fruit like banana or apple. Certified organic."

Pros: "Boarding system efficient. Lots of leg room. Choice of snacks. Good service."

Pros: "Entertainment on board"
Cons: "My flights was delayed"

Pros: "Gave me my refund!"
Cons: "Flight was delayed 5 times without sufficient reason. Weather was clear. Had to ask for a refund after the 6th delay. Missed an important event."

Pros: "Extra leg room"
Cons: "On both legs of our vacation, going and coming we experienced long delays , 2 hours Boston.to Vhicago and 3 hours Chicago to Boston"

Pros: "This was my first time with JetBlue and I was pleasantly surprised with the size of the plane. It was pretty comfortable"

Pros: "Friendly staff and the on board entertainment and snacks"
Cons: "The last time I took JetBlue the flight was delayed by almost 3 hours"

Pros: "the plane was good!"
Cons: "the plane boarded late"

Cons: "Great trip!"

Pros: "Great social distancing and Delta supplies MULTIPLE sanitizing options!!"

Cons: "My sister’s checked in luggage was in poor shape when we got it in Albany. We noticed an outside compartment was unzipped. So we checked to see if anything was missing and a souvenir from Mexico was gone. Then we realized a zipper was missing from the luggage and then decided to check all the other compartments and realized her bag of jewelry was gone. The woman at baggage services in Albany told us Delta is not responsible for lost belongings. Also tried to tell us theft is not an issue because there are cameras everywhere. Well you are telling someone that is missing a bag of jewelry that theft is not a problem. Also, there may be cameras everywhere but I doubt anyone is going to review those cameras to see what happened. I will never fly Delta again."

Pros: "Crew was super helpful and very accomodating"
Cons: "Can’t think of anything. A few times I’ve flown Delta, the service has improved. Having helpful staff on board is very important . Years ago it was very unpleasant to fly Delta because of rude flight attendants especially on us domestic flights. Hopefully that has all changed. Especially the older crew. If they can’t stand doing better customer service they need to retire . Happy to fly Delta and will let people know."

Pros: "Just ok"
Cons: "update the gate info correctly and immediately. I was directed by app to go B5A but actually it is B5 gate in SEA-TAC"

Cons: "Flight cancelled with no reasonable alternative. Ended up driving."

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "I liked the crew."
Cons: "I didn’t appreciate the women at the boarding counter. She had a very bad attitude and was not approachable."

Pros: "Very comfy first class seats"

Pros: "Loved the plane, people and timeliness"

Pros: "Crew was nice and tried to help us as there was no food on board for our dietary restrictions."
Cons: "The folks at the desk arrived late to address issues. It was crowded and disorganized. When i addressed an issue at the check in regarding not seating me with my children including a 7 year old). the response is. Well you bought a cheap flight so tough luck. The plane was dirty and frankly not very"

Pros: "I love that they have food on long flights and I get an hour of free WiFi because I have T-mobile."
Cons: "Small seats but I’m tall so I have to live with it."

Cons: "At least one hour late"

Pros: "Plenty of room and friendly service was refreshing for such a long flight"

Pros: "Comfortable, not-overstuffed plane, friendly crew, excellent service, lots of good food & snacks. Travel as it used to be."

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Cons: "No entertainment options at all."

Pros: "Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment"
Cons: "Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable"

Pros: "codeshare by China Southern"
Cons: "codeshare by China Southern"

Pros: "The flight crew was so nice! Roomy seats and plenty of snacks!"

Pros: "On time"

Pros: "I arrived safely."
Cons: "We all were bused to the plane. And we all had to stow our carry on bags with checked luggage."

Pros: "Got to London on-time (early, actually) and safely. The in flight meal was okay. The leg room in comfort plus was great, the mobile app was awesome, and the staff (check-in, gate, cabin and flight deck) were professional and friendly all around."
Cons: "The leg room was great, but as a broad-shouldered guy, the width of the seat was miserable. Unfortunately, the Delta 767 doesn't offer any upgrade for a wider seat beyond Delta One, and my employer won't spring for that. Too bad there isn't a premium economy option. Also, the entertainment unit in the seat next to mine malfunctioned, which you wouldn't think would impact me that much except that because it was "seeing" touches randomly throughout the flight, the screen would turn on, off, brighter, dimmer, play random stuff, and just generally be as annoying as possible to everyone nearby throughout an overnight flight."

Pros: "Crew were helpful and pleasant"
Cons: "Seating was uncomfortable, cabin was cold and no blankets available, food was just ok, plane had lots of empty seats yet everyone was squeezed into 3 in a row making it uncomfortable, no updates from captain or crew as to where we were in the flight....."

Pros: "On time boarding, quick, friendly staff, extremely helpful"
Cons: "Gate should be bigger to seat all passengers patiently waiting. Was a mess of people sitting all over the floor"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "Delta gate agents kept everyone well informed and updated as to new boarding time/procedure"
Cons: "Flight was delayed by 4 hours and reason was not explained or obvious"

Pros: "The snacks were decent on the flight. Everything else was a disappointment."
Cons: "Unexpected delay for take off after being told the flight was going to be on time. They couldn’t give us a reason or an eta on take off while waiting at the gate which affected my ride situation once I landed in Seattle."

Pros: "Everything was great. Very nice flight"
Cons: "No complaints"

Pros: "Nothing"
Cons: "Before was better no now"

Cons: "Overall the flight was good. It would be nice to see if we are Lincoln and Wi-Fi and the greatest selection of movies to its offerings."

Pros: "On time with early arrival"
Cons: "Small plane Little communication from crew Security took forever to get through at RC airport"

Pros: "Service was fast and the inflight entertainment is free. Lots of movies to chose from, which is nice for the long flight."
Cons: "It was the most cramped I have ever felt in a plane and also the longest flight. Horrible combination. Some of the crew were snippy."

Pros: "Flight arrived early!!"

Pros: "Flights were on time and friendly attendants!"

Pros: "Everything"
Cons: "Nothing"

Cons: "waiting on the tarmac for 40 minutes"

Pros: "Many thanks to Delta for changing our flight at an even exchange to get us out of Florida before the storm. I will fly delta again."
Cons: "Old plane to and from San Antonio. New planes make for a more comfortable ride"

Pros: "The new delta seats are super uncomfortable and zero legroom. When you put the seat back back the butt part goes forward and your knees are crunched in front of you. The cushion also angles down its horrible. They gave a couple rows extra room and now charge more for them while crunching every other seat together."
Cons: "Seats and legroom horrible"

Pros: "Fast boarding, everyone nice."
Cons: "Wifi was yo and down the whole flight, about 20 times, so kids were not entertained."

Pros: "Just over 2hrs only. Crew was very friendly."
Cons: "A bit of turbulence due to weather (no fault of the airlines)."

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "The crew was nice. It was a pretty smooth flight."
Cons: "The entertainment system didn't work. Very long flight to not have entertainment. No plugs for personal devices. It looked like an older plane."

Pros: "I fly Delta Airlines 2x a year and if I had to go on this flight experience alone I would never fly with them again. This particular flight attendant. Brunette who wore all red~ like she had a personal conflict with us from the moment we walked on the plane. We were sitting in the back and could hear the things that she was saying about my grandson and myself. She was rude, snotty, had a sassy mouth. I was COMPLETELY APPALLED as to the way we were treated by her. It was a long flight to have someone you felt was bullying you the whole flight to the moment we were exiting the plane. Karma will come back to her one day..."
Cons: "I fly Delta Airlines 2x a year and if I had to go on this flight experience alone I would never fly with them again. This particular flight attendant. Brunette who wore all red~ like she had a personal conflict with us from the moment we walked on the plane. We were sitting in the back and could hear the things that she was saying about my grandson and myself. She was rude, snotty, had a sassy mouth. I was COMPLETELY APPALLED as to the way we were treated by her. It was a long flight to have someone you felt was bullying you the whole flight to the moment we were exiting the plane. Karma will come back to her one day..."

Pros: "Not too much this leg!"
Cons: "Baggage retrieval was horrendous! Absolutely a nightmare which after paying for 3 nights hotel with no discount, I was further inconvenienced by the inability to receive my 2nd luggage and after requesting it be delivered, I, I, tracked my bag and you chose to send it 3 days ahead to my destination and I HAVE NOT RECEIVED any acknowledgment of my online inquiry which is why I am complaining. I've had to purchase a new set of luggage AND will have to pay for them on my next 2 legs on Delta. I apologise for seeming so harsh as I know you've had so much trouble because of the tornadoes, but this leg of my trip cost me an additional $800.00 plus AUD and I was here in the US to care for my father who recently had a 2nd heart attack and my final days in USA were meant to be a holiday, and all I can say is the stress because these expenses have removed any enjoyment (I know I'm looking at this half empty, not half full). I'm glad to share this and hope you're company loses will be recouped after this mess! Daniel Grayson Craigieburn, VIC Australia"

Pros: "I was notified about the delay via text before I left for the airport, which was nice. I would not have checked my email."
Cons: "Delayed for over 2 hours. I have never flown Delta before this flight and it wasn't a great representation. The flight attendants were nice but I was in a seat near the engine and it was making really weird noises. I fly almost every two weeks, so I'm used to engine noises but this was one of the loudest/most rickety sounding flights I have ever been on.. and I have flown Spirit a few times. It just didn't feel safe. Landing scared me a little too as I have landed in O'Hare countless times and have never flown so low to the highway upon entry. It felt like we were only a couple hundred feet above the cars."

Pros: "The pilot was funny and flight crew was friendly."
Cons: "What I didn't like was out of their control!"

Pros: "Clean comfortable plane, timely service by crew. Good,comfortable, economy seating in the A330 plane."

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "Crew members were okay"
Cons: "Wifi could be better"

Pros: "Good friendly and efficient crew"
Cons: "Boarding process was poorly executed so 3 and 8 were called simultaneously"

Pros: "Very friendly and accommodating."
Cons: "tv screens on the back of seats"

Pros: "The ground crew worked really hard to get us going."
Cons: "The flight was delayed 1.5 hours."

Pros: "Crew"
Cons: "DCA poorly organized"

Pros: "Nothing."
Cons: "You could have been on time. You could be accountable. You ruined my wife’s 40th birthday by failing to fulfill you’re end of the deal."

Cons: "How about departing on time! Almost 3 hours after our advertised departure time is ridiculous!"

Pros: "The crew was fantastic and very nicely got us into an earlier flight and allowed my wife and I to sit together for our 10th anniversary"
Cons: "The entertainment apps were difficult to use"

Cons: "Many of the crew members seem as if they hated their jobs. I hesitate asking them anything."

Pros: "Easy boarding, smooth flight, friendly staff."
Cons: "Small plane, kept hitting my head on overhead bins"

Pros: "WiFi entertainment system."
Cons: "Hard seats, no arm padding. No power to recharge phone and iPad."

Pros: "Nothing. This was the worst flight I’ve ever been on."
Cons: "Pretty much everything. The flight was delayed for mechanical reasons. Then they boarded us and we sat for 3 hours on the tarmac because one of the air conditioning packs was broken. When we finally arrived, I found out my bag was lost. The worst flight of my life."

Cons: "Most everything could have been better. All phases were far below average."

Pros: "Everything BUT the ticket agent"
Cons: "Key West Ticket agent who also did double duty as boarding agent was so rude and condescending to everyone. Very short and impatient. Speaking to us like we were all idiots. Employees like him give flying a bad rap."

Cons: "The online information was inaccurate on where the pet relief areas were located and I nearly missed my flight as a result. Need to install more ESA /Supprt animal relief areas to make It more friendly to travelers. Very stressful experience overall"

Pros: "The crew and the service"
Cons: "The seat I have had 13C for the last 3 flights to and from Miami on this plane has the controller broken where it does not stay in place and pops out. This time a soda was spilt on the seat, and the steward had to change the seat out for a clean and dry one.this plane has no entertainment displays other than the general cabin ones and this one is out of focus and the colors are blurred."

Cons: "Delayed for more than 2 hours, at midnight, then more delay over the plane"

Cons: "The sound on the entertainment system in my seat didn't work well. Also, the flight was really late getting in to Denver."

Pros: "Flight was on time."
Cons: "It’s a commuter. It’s tiny. In flight left trash with us till plane was about to land. Pilots seemed inexperienced. Landing was hard, braking was hard approach was awkward and it was a beautiful day with no wind. Pilot shortage isn’t helping the regionals."

Pros: "Flight was smooth"
Cons: "Nothing"

Pros: "Departure was on time"
Cons: "Really hard seats, no phone charger outlets, on board WiFi didn’t work"

Pros: "For me, a flight is “excellent” anymore if it’s on time and no one gets booted off the plane. Both flights were early!"
Cons: "Didn’t look he the free snacks."

Pros: "We got to our destination aver 12 hours late."
Cons: "In addition to being rebooked approximately 12 hours after our original flight, this flight left about 40 minutes late."

Pros: "Leg room. Crew. Nice airplane. Even captain greeting passengers."

Pros: "Delays, delays, delays. An initial delay of 1.5 hours due to a switched plane. Then they needed mechanics to check out a bird hit to the plane. That took another 3 hours to happen. And they boarded us first, then found the issue, deplaned us, had a gate switch and then the wait. Very frustrating! Once on board, everything went smoothly as it typically does."
Cons: "The long delay"

Pros: "Arrived slightly early. The crew was efficient and friendly. The interior and seats looked new."
Cons: "Nothing was negative."

Pros: "I arrived in Sydney the day I was supposed to. Everything else was a let down and was not what I paid for."
Cons: "American Airlines cancelled a flight because of ‘weather’ from Msy to dfw, all other flights from Msy to Dallas operated on time but were sold out. We were re booked flying through San Francisco, missing out on flying on qantas, which is what I had paid for since they are a premium airline. We were booked on virgin America and then United for the international flight. United charged us each for 2 bags totalling $150 each, despite we booked a ticket with qantas which allows 2 bags each. Virgin America honoured our 2 bags, but united refused to. United also has service and aircraft which do not match the levels of qantas which I has specifically sought out. I could not eat some of the food because of the poor quality, and this is something I’ve never done before on an international flight. Additionally their were a lack of amenities on both flights, and no food vouchers despite our travel delay of over 5 hours. This whole ordeal has cost me money, worktime, and created a lot of stress to where I have had to cancel meeting on my arrival in Sydney."

Cons: "No free wifi"

Pros: "Ensured that the connecting passengers boarded the flight."

Pros: "seating assignment"
Cons: "wish the crews were more pleasant. some were pretty rude to some passengers"

Pros: "efficiency of terminal and flight changes at Dallas-Fort-Worth excellent. valet service and complimentary checked standard carry-on bag."
Cons: "Didn't know about close connections and terminal changes until printing boarding passes. Snack offerings are minimal one almost all airlines for regular fares. a tiny wafer cookie or about 5 mini-pretzels are not very impressive. I wold much prefer peanuts to pretzels--an option would be good. The gate of outgoing flight to Bloomington kept changing on phone m messaging shortly before takeoff , about 6 gate changes in 10 minutes. Confusing!"

Cons: "Coach seating is too tight"

Pros: "The cabin crew was great at boarding and organizing the overhead bin space. Also, ground staff didn’t start check roll aboards before the overheads bins were full. There is nothing more frustrating than getting on after forced to gate check your bag to empty bin space (ahem, United at SFO)."
Cons: "Couldn’t get the entertainment to work."

Cons: "Boarding chaos at Miami airport."

Pros: "Everything was great about my flight from Buffalo. Friendly people, easy boarding and flight was smooth as I expected."

Cons: "Not so pleasant flight attendants."

Cons: "Flight was delayed 8hours"

Cons: "The check in process at JFK was a disaster. The kiosk check in machines were constantly malfunctioning, where to line up was unclear, and staff acted frustrated. After several failed attempts with the kiosks you have to wait in line to check in at the counter anyways. It would have saved almost an hour of my time to just go straight to the counter-- had I been allowed to. I wanted to check a bag which contained some fragile items. Several bottles of wine which I wrapped in bubble wrap and cushioned with my packed clothes. I requested a "Fragile" sticker to be put on my bag. I was told "We don't do that here". So I asked if they handle ALL bags with extreme care and I was laughed at and told to go on my way. When I got my bag at my destination-- the outside of my leather suitcase was sliced to the lining. There were scuff marks and torn leather. My wine had been completely shattered. Not just a crack in the bottle, but flattened completely. My clothes were stained, my bag ruined. I don't know if putting a fragile sticker on would have prevented this, but I don't understand why they just "don't do that". We are trusting our property to the airline when we check bags. I will never trust American Airlines ever again. They don't want to know if I have anything fragile, and they don't care when I tell them."

Cons: "After everyone boarded they said they had a 2 hour delay and if you got off the plane your flight would be cancelled. After an hour of sitting on the plane they got everyone off so a different plane could board and take off and then everyone got back on the plane and continued to wait. We left 2.5 hours late and when we arrived at the destination the plane couldn't contact the tower?!?! So we waited another 30 mins...ridiculous, rude, and rather fly southwest"

Cons: "Staff was rude and accoutable for delayed flight and lightning striking plane while we were in the air"

Cons: "I am missing two items that I had in my checked bag and my clothes and belongings were all messy as if it had been gone through. I am very upset that these items were likely taken by whoever went through my bag."

Pros: "On time"
Cons: "Comfort"

Cons: "It was delayed because of late or no show flight attendants. Thankfully two women who just got done offered to do the flight, so our flight wasn't cancelled."

Pros: "Smooth takeoff and landing no turbulence.no issues at baggage claim.I boarded later and had to gate check because overhead bins were full."

Pros: "Good pilot communications. On time departure and arrival."
Cons: "Very cramped quarters. Broken seat. Out of control heating system. Rude staff An hour wait for baggage."

Pros: "Fabulous crew and service, absolutely fantastic."
Cons: "Having to get off!"

Pros: "The flight attendants were courteous and the ride was very smooth, I felt at home."
Cons: "We received no snacks coming back home to Jamaica but we give thanks for you guys informing us."

Pros: "Nice landing."
Cons: "Leg room"

Cons: "Price"

Pros: "Snacks were good. Staff was nice and accommodating."
Cons: "Plane was old and uncomfortable. Part of the paneling in the wall wasn't lined up and looked like it was cracked and loose. Dear pocket back was falling off and my tray table was cracked and leaned towards one direction."

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Illinois to Grand Cayman

Airlines flying from Illinois to Grand Cayman have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Illinois to Grand Cayman

Mandatory masks

Masks required on board, masks provided on flights from Illinois to Grand Cayman

Social distancing seating

Middle seats unavailable to book on flights from Illinois to Grand Cayman

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Illinois to Grand Cayman

Book cheap flights from Illinois to Grand Cayman

Recent round-trip flight deals

9/19
Sun
1 stop
JetBlue
6h 21m
ORD - GCM
9/25
Sat
1 stop
JetBlue
9h 42m
GCM - ORD
10/30
Sat
1 stop
Multiple Airlines
6h 15m
ORD - GCM
11/6
Sat
1 stop
Multiple Airlines
12h 02m
GCM - ORD
8/7
Sat
1 stop
Multiple Airlines
11h 25m
ORD - GCM
8/14
Sat
1 stop
Multiple Airlines
11h 14m
GCM - ORD
8/3
Tue
1 stop
Multiple Airlines
10h 30m
ORD - GCM
8/23
Mon
1 stop
Multiple Airlines
22h 53m
GCM - ORD
8/3
Tue
1 stop
Multiple Airlines
10h 30m
ORD - GCM
8/17
Tue
1 stop
Multiple Airlines
11h 14m
GCM - ORD
8/4
Wed
1 stop
Multiple Airlines
28h 42m
ORD - GCM
8/18
Wed
1 stop
Multiple Airlines
6h 49m
GCM - ORD
8/9
Mon
1 stop
Multiple Airlines
15h 05m
ORD - GCM
8/23
Mon
1 stop
Multiple Airlines
22h 53m
GCM - ORD
8/8
Sun
1 stop
Multiple Airlines
22h 50m
ORD - GCM
8/23
Mon
1 stop
Multiple Airlines
22h 53m
GCM - ORD
8/7
Sat
1 stop
Multiple Airlines
11h 25m
ORD - GCM
8/21
Sat
1 stop
Multiple Airlines
11h 14m
GCM - ORD
10/25
Mon
1 stop
JetBlue
6h 21m
ORD - GCM
11/1
Mon
1 stop
JetBlue
9h 55m
GCM - ORD
8/3
Tue
1 stop
Delta
7h 00m
MDW - GCM
8/22
Sun
1 stop
Delta
9h 25m
GCM - MDW
8/6
Fri
1 stop
Delta
7h 00m
MDW - GCM
8/18
Wed
2 stops
Delta
18h 58m
GCM - MDW
6/29
Tue
2 stops
American Airlines
49h 14m
BMI - GCM
7/3
Sat
2 stops
American Airlines
20h 08m
GCM - BMI
6/1
Tue
2 stops
American Airlines
42h 08m
MLI - GCM
6/5
Sat
2 stops
American Airlines
19h 57m
GCM - MLI
6/29
Tue
2 stops
American Airlines
49h 14m
BMI - GCM
7/3
Sat
2 stops
American Airlines
25h 33m
GCM - BMI
6/1
Tue
2 stops
American Airlines
42h 08m
MLI - GCM
6/7
Mon
2 stops
American Airlines
27h 07m
GCM - MLI
8/28
Sat
1 stop
Delta
7h 00m
MDW - GCM
9/2
Thu
1 stop
Delta
9h 25m
GCM - MDW
8/28
Sat
1 stop
Delta
7h 00m
MDW - GCM
9/3
Fri
2 stops
Delta
18h 58m
GCM - MDW
8/25
Wed
1 stop
Delta
7h 00m
MDW - GCM
9/5
Sun
1 stop
Delta
9h 25m
GCM - MDW
6/29
Tue
2 stops
American Airlines
49h 14m
BMI - GCM
7/3
Sat
2 stops
American Airlines
20h 08m
GCM - BMI
Show more results

Recent one-way flight deals

10/30
Sat
1 stop
Delta
17h 45m
ORD - GCM
10/30
Sat
1 stop
Delta
17h 45m
ORD - GCM

Search by stops

Search by airline

Search by price

-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First